A Conversation with Nick A. Olivero & Bennett Fisher, writers of San Francisco’s The Speakeasy

If you’ve spent time exploring the Bay Area theater scene over the past few years, chances are you know—and love—The Speakeasy; it’s a one-of-a-kind immersive experience that sends audiences back in time to the sumptuous world of the 1920s. The production has been thrilling audiences since 2014 with its unique storylines, intricate staging, and fun interactive elements.

We caught up with Nick A. Olivero and Bennett Fisher, the writers of The Speakeasy, to learn about their inspiration for the production, the process of developing so many unique characters and storylines, and why The Speakeasy is basically “Boardwalk Empire meets Westworld.”

Photo Credit: Peter Liu

Can you talk about your inspiration for The Speakeasy?

Nick: I originally had the idea in 2005 while I was in tech for another show. It sort of just popped into my head at 2 AM without any rhyme or reason. I’ve always been a fan of Vaudeville entertainment and blurring the lines of reality and fiction, and I thought having a cabaret and casino would make for a fun night out.

Bennett: Nick is really the creative force behind this one. He’d built up a reputation for doing ambitious projects in the more traditional, proscenium theater vein, so it didn’t surprise me when he announced his intentions for the first version of The Speakeasy back in 2014. That initial production was a massive success, and Nick and the other producers wanted to bring it back on a bigger scale. I wrote some scenes for the 2014 production, and they brought be back to help Nick compose this new version.

What was the writing process like?

Nick: The process changed over the course of four years of writing and rewriting the show. The first development meeting started in 2013 with about six people and a huge wall of blank paper. I asked the question, “What sort of people would be at a 1920’s speakeasy?” For the next hour we spitballed out about 60 characters. We ended up keeping about 50 of them and, to this day, they are still in the show. We then created a “web,” giving characters multiple connections to one another and a major storyline as well as secondary storylines. When the show closed in June of 2014, everything was on the chopping block. This time, I created a flow chart called “The Speakeasy Timing of Events”, which is a play-by-play of what happens in the show. Having six rooms perform simultaneously and characters entering and exiting from room to room, the timing had to be planned precisely. After all of these marathon meetings, I’d have phone calls with Ben to discuss everything that came up. I’d rough out the storylines and scenes and then he’d go and write a first draft of the scene. From there it became a ping pong game of sending scenes back and forth to be edited and polished, and sometimes completely overhauled.

I would say that the writing process very much mirrors the same disorientation audience members feel when coming to the show. It was all a bit of a blur, but completely exciting. Ben and I are still rewriting scenes and adding in new bits as actors have ideas or I see something happen impromptu at the show. We keep building and rebuilding, giving audiences something new and entertaining each time.

Bennett: Going in, we had some things from the 2014 production to use as inspiration – some characters, a few pieces of storyline – but that was more of a starting place than anything else. Nick and I would talk through the big ideas; it’s really his world, so he would direct that conversation. Some of that discussion was about the larger themes of the piece, and the broader arc of a character’s journey throughout the night. I was in grad school in San Diego for most of the writing process, so we talked a lot on the phone! A few ideas came from us just joking around and doing improv. After we were both satisfied with the drafts, we’d read them aloud with actors, get group feedback, and, of course, make sure they clocked in at the right time. There’s over 1,500 pages of dialogue in the show, so it was truly a massive undertaking. And we’re still tweaking it!

Photo Credit: Peter Liu

Do you have a favorite character or scene?

Nick: There are so many wonderful characters in the show to get to know. Most audiences love the tragic tale of Velma, the resident chanteuse, but I think Ben and I both really liked writing for Cliff and Leland. Ben wrote their five original scenes in the first show; they were standalone side characters with no real arc. For the remount, they became integral, providing a great sense of comedic relief. They are audience favorites for sure. Ben would write a scene [for them] and then I would add to it, then he would add to what I wrote, and back and forth we would go, laughing as we kept thinking of their ridiculousness and idiocy. The guys get away with murder because they are lovable….but boy are they dumb!

Bennett: I have a lot of favorite characters. I have a soft-spot for Cliff and Leland because I wrote one of their original scenes in 2014. I like Dorothy and Vivian, because they both have a very wicked, cutting sense of humor. I like Mac, because it’s always fun to write a character that’s laconic in a world where everyone else talks fast. I like the Wizard of Oz scene in the dressing room, Floyd’s entrance, Dorothy’s monologue. But every time I’ve seen the show, it’s wonderful to see how each actor makes the character individual or finds a new dimension of a moment. The show is so much more than just the dialogue – you’re watching life transpire all around you. It truly surprised me when I first saw it all together – it doesn’t feel like a play, you actually feel like you’re going back in time.

How would you describe The Speakeasy to someone who’s never been?

Nick: I usually describe it as Boardwalk Empire meets Westworld. If that doesn’t mean anything to the person, I say it’s like a giant choose-your-own-adventure. Most audiences have no idea what to expect, and I’m okay with that.

Bennett: It’s a trip back in time to 1923. You get the experience of going to a ’20s gin joint, with the added bonus of being able to step inside the mind of the characters from time to time. It feels both like memory and a dream.

Photo Credit: Peter Liu

What makes The Speakeasy a truly unique night of theater?

Nick: Where else can you watch a Vaudeville cabaret, gamble at a casino, spy on a dressing room through a two-way mirror, get pulled into audience interaction and one-on-one’s, all while holding a killer prohibition style craft cocktail in your hand?

Bennett: It’s very tactile. You’re not a passive observer, you’re dropped into a world. It’s also just a great party – I like the social dimension a lot. You can enjoy a cocktail, play a round of blackjack, and watch a scene. You become part of the world. It’s impossible to tell who is an actor and who’s an audience member until a scene begins. And you can curate your own experience.

Is there a specific anecdote from The Speakeasy’s run that stands out in your memory?

Nick: The environment allows for incredible impromptu moments. We’ve had proposals on the stage during the show, birthdays, anniversaries, bachelorette parties. This show allows people to be transported to another time and assume different roles if they want to. But it also does what any good piece of theater should do: it holds a mirror up to society and gives the opportunity for self-reflection and acknowledgment. I was playing Harold for a short run; he is a closeted homosexual. I pulled a young man into a room for a one-on-one encounter. During the experience, I described my challenges of not coming out during my lifetime, admitting that in the large scope of things it just didn’t really matter. I find out the next day that he left and had a conversation with one of our security guards (this guy is not in the show at all, he just guards the door), and it turns out that the patron came out to him! I never got to talk to him about it, but I had no idea what he was struggling with when I pulled him in – it was fairly random. Moments like that happen all the time in the show. And for the actors it’s better than a curtain call!

Bennett: I wasn’t able to really watch the show in rehearsal, so I first experienced it in an invited preview performance before our official opening. I remember that moment of stepping into the bar: the quality of the light, the tinny music from the speakers, all the little details about the atmosphere. I knew the story, but I didn’t fully appreciate the experience until that moment. I really felt like I was in another world. They ask you to put your phone away for over three hours when you come, and I never felt the urge to reach for it. When you’re there, you’re fully present, and it’s a wonderful thing.

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